ChemInform Abstract: Synthesis of Indazole Motifs and Their Medicinal Importance: An Overview

Gaikwad, Digambar D.; Chapolikar, Archana D.; Devkate, Chandrashekhar G.; Warad, Khandu D.; Tayade, Amit P.; Pawar, Rajendra P.; Domb, Abraham J.

doi:10.1002/chin.201512320

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2018

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“…Tetrahydroindazoles play an important role in medicinal chemistry and depending on envisaged structural modification can be regarded either as annulated pyrazole analogs [1] or as partially saturated indazoles [2]. Recently, tetrahydroindazole derivatives have been used as peripherally selective cannabinoid-1 receptor inverse agonists [3], sigma-2 receptor ligands [4], and interleukin-2 inducible T-cell kinase inhibitors [5].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Tetrahydroindazole-Triazole Conjugates and their Derivatization by the Ritter Reaction

Namsone

Rībena

Turks

2018

KEM

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7-Azido-3,6,6-trimethyl-1-(pyridin-2-yl)-1,5,6,7-tetrahydro-4H-indazol-4-one undergoes copper (I)-catalyzed 1,3-dipolar cycloaddition reactions with terminal alkynes and provides the corresponding 7-(1H-1,2,3-triazol-1-yl)-derivatives with excellent yields. Reduction of keto group at C(4) gives an access to diastereoisomeric mixture of alcohols. The latter provide acetamides in the Ritter reaction with acetonitrile upon treatment in acidic media. The developed synthetic sequence offers an easy entry into 4,7-difunctionalized tetrahydroindazoles which are interesting in terms of medicinal chemistry.

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